Learn to Pitch From Battle-Tested Entrepreneurs | The Garage Group

Learn to Pitch From Battle-Tested Entrepreneurs

A financial services team with which we’re partnering entered into the final phase of their 12-week Lean Innovation Bootcamp—it was time to learn how to pitch from battle-tested entrepreneurs. We put together a diverse panel of experienced entrepreneurs to give them advice before the team prepared their own pitches.  

Our panelists included:

Here are some lessons that they shared on how they learned—through some of their worst pitches–how to effectively pitch:

Take the Scary Meetings: Taking meetings and pitches with more intimidating people might mean that you have a lower chance of being successful, but provide more opportunity to improve future pitches.

“When we were just starting, we were talking to this really smart VC, and he asked, “So how are you going to beat your top competitor?” And I had no answer to that question. It is a question that I’ve thought about for two years—that is THE question. Take the meetings with the scary people, and go get your ass kicked, because that is how you get better.” – Ry Walker

Know your Audience: When you’re formulating your pitch, you need to know who you’re trying to influence. People will ask questions regarding the risks most related to their backgrounds.

“On one of my worst pitches, I didn’t do enough due diligence up front to understand that they’d previously had a market research company (same category as KnowledgeHound) they’d invested in that had completely bombed. So when we got in there, they just hammered us on the marketplace, and how everything was wrong with market research. I don’t even know why they’d taken the pitch. I walked in the door without even having a chance.”  – Kristi Zuhlke

Control the Story: Losing control of the story can cause you to lose your momentum. All of a sudden, you’re playing catch up to questions instead of controlling the narrative.

“Somehow, we were five minutes in and they got stuck on a feature in our product. And we walked out of that, both dazed and confused, asking ourselves what happened. But it was an important lesson for us, because we’d jumped right into the features, the “how” behind what we were doing, and not the “why”, or what problems we were solving, and it took us out of our groove; we lost control of the story. All of a the sudden we were playing catch up to their questions instead of us driving the conversation.”  – Darrin Murriner

Learn from Your Worst Pitch: The worst pitches can be the ones you learn from the most. If you receive questions that derail your pitch, or share content that doesn’t strike interest for your audience, evaluate, pivot, and try again.

“Your very first pitch, is like an art class in school, going back really far in your artwork, something you did in third grade isn’t going to be as good as something you did recently.” – Matthew Dooley


Thanks to Kristi, Darrin, Ry, & Matthew for sharing their sage advice from their past experiences, and helping our teams improve their ability to pitch to senior leaders. To learn more about pitch training, and TGG’s Lean Growth Bootcamps, check out this case story about our partnership with a F100 Financial Services company.


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